Holiday rentals in Windham

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Top-rated holiday rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham
4.99 out of 5 average rating, 317 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Guest favourite
A charming retreat is nestled among trees, featuring a spacious deck that overlooks the calm waters. The property's exterior is a blend of blue and white, with steps leading down to the dock area. Two kayaks are visible near the water's edge.
Home in Atkinson
5 out of 5 average rating, 8 reviews

NH Lakeside Island Retreat

Chase Island is perfectly situated on Big Island Pond. This island retreat offers 270 degree water views. Outdoors you will find a large deck, dock, and calm waters to enjoy a peaceful swim. Step inside and you will find an open area with gorgeous water views. The eat in kitchen and living room combination allows guests to spend quality time together. Two bedrooms fully equipped proving guests with rest and relaxation. No lifeguard, swim at your own risk. No fires. Quiet time is 10 PM.

Guest favourite
An aerial view showcases a spacious property surrounded by lush trees, featuring a large private tennis court and half-basketball court. The well-manicured grounds are complemented by additional outdoor areas, highlighting a serene and inviting environment.
Home in Windham
4.93 out of 5 average rating, 321 reviews

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

Top guest favourite
A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.
Guest house in Salem
4.93 out of 5 average rating, 135 reviews

Lake Front Private Guest House in So. NH

Just 36 miles north of Boston/Logan Airport. Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen/1 full) w/additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park, Tuscan Village & 5 popular wedding venues. Short drive to So Maine, NH seacoast, white mountains & foliage.

Guest favourite
A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.
Flat in Windham
4.89 out of 5 average rating, 361 reviews

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

Guest favourite
The dining area features a wooden table surrounded by four high-backed chairs. A large piece of artwork is displayed on the wall, and a potted plant adds a touch of greenery. The open kitchen is visible in the background, equipped with modern appliances.
Flat in Derry
4.87 out of 5 average rating, 127 reviews

3 Bedroom Apartment in Downtown Derry

Cozy up during your next trip to southern NH! Built in 1910, this apartment has been completely renovated. Meadowview is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Superhost
A modern kitchen features white cabinets and sleek stainless-steel appliances. A central island with a wooden countertop provides seating for one. Natural light filters through a window covered with sheer curtains, illuminating the space with a refreshing ambiance.
Home in Salem
4.86 out of 5 average rating, 63 reviews

Great for Families Modern Farmhouse Near Shopping

Beautifully renovated, Salem, NH 3bd, 3ba farmhouse, where rustic charm meets modern comfort. Centrally located, just a short walk from Tuscan Village & Rockingham Mall. Near two major highways, (93 & 495). Whether you're planning a day trip to Boston (40 min) or exploring Manchester (30 min), you're in the heart of it all. Canobie Lake & scenic hiking trails are within a stone's throw, & ski slopes 30-min. Ample parking. With 3 bdrms, this spacious retreat can accommodate up to 8 guests.

Guest favourite
The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.
Farm stay in North Andover
4.95 out of 5 average rating, 296 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Top guest favourite
A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.
Guest suite in Tyngsborough
4.98 out of 5 average rating, 269 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

Superhost
A sandy beach area is visible, bordered by lush green trees, leading to a tranquil lake. The calm water reflects the clear blue sky, while scattered boats are moored along the shoreline. Sunlight filters through the leaves, creating dappled shadows on the sand.
Cottage in Windham
4.83 out of 5 average rating, 53 reviews

Quaint Cobbetts Pond Cottage with Pond Views

A cute, clean & cozy, one bedroom cottage on Cobbetts Pond in Windham NH. The cottage is a few feet from a shaded, private community beach and you can view the sunrises each morning over the pond. The cottage is well appointed and the entire place is yours to enjoy There are tons of hiking trails nearby & the lake is clear and perfect for swimming and canoeing in the provided canoe! We are less than an hour drive from Boston & the beach. House was built in 1934

Top guest favourite
Dome in Sutton
4.96 out of 5 average rating, 151 reviews

Luxury Glamping NH - Geodome Sanctuary

Escape to a private luxury sanctuary retreat tucked behind a charming Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 90 minutes from Boston, yet a world away.

Guest favourite
A rustic cabin features a fire pit surrounded by multiple chairs, inviting outdoor gatherings. The wooden structure showcases earthy tones, nestled among trees with colorful foliage. Tiki torches are positioned nearby, enhancing the cozy atmosphere for evening relaxation.
Cabin in Windham
4.9 out of 5 average rating, 165 reviews

Little Lake, Big Fish - Fire Pit & Pvt Beach

@DiamondHomeCollection on Insta Please read Other Details To Note Our area is full of life and peace. Wake up to the loons early in the morning and go to bed listening to the owls. Watch the turkeys cross the yard. Our homes are from the 1920's, we keep them alive and for the souls who love old homes. 45 minutes to the ski destinations ocean, lakes region, and hiking. Not waterfront, we own shares of waterfront. And spring

Popular amenities for Windham holiday rentals

When is the best time to visit Windham?

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Avg. price€113€109€109€109€122€131€142€145€129€117€109€113
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Frequently Asked Questions

  • Where should I stay in Windham?

    Make yourself at home in Windham by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in West Windham, and over 20 vacation rentals in Windham Depot.

  • Are there pet-friendly vacation rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Windham?

    Yes! Work meets play with ease at over 30 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Windham?

    Windham has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Windham?

    Experience the best of Windham with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Windham have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Windham

  • Total holiday rentals

    Explore 50 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 3,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Windham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Windham rentals

  • 4.8 Average rating

    Windham stays are highly rated by guests – averaging 4.8 out of 5!